HUT61050A - Process for producing and applying enzymes - Google Patents

Process for producing and applying enzymes Download PDF

Info

Publication number: HUT61050A
Authority: HU; Hungary
Prior art keywords: lipase; isoenzyme; esters; acid; csc
Prior art date: 1989-06-05

Application number

HU904853A

Other languages

English (en)

Hungarian (hu)

Other versions

HU904853D0 (en

Inventor

Carrington S Cobbs

Michael J Barton

Lin Peng

Animesh Goswami

Adrien P Malick

John P Hamman

Gary J Calton

Original Assignee

Rhone Poulenc Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-06-05

Filing date

1990-06-01

Publication date

1992-11-30

1990-06-01 Application filed by Rhone Poulenc Inc filed Critical Rhone Poulenc Inc

1992-02-28 Publication of HU904853D0 publication Critical patent/HU904853D0/hu

1992-11-30 Publication of HUT61050A publication Critical patent/HUT61050A/hu

Links

238000000034 method Methods 0.000 title claims abstract description 205
230000008569 process Effects 0.000 title claims abstract description 113
102000004190 Enzymes Human genes 0.000 title claims description 130
108090000790 Enzymes Proteins 0.000 title claims description 130
108090001060 Lipase Proteins 0.000 claims abstract description 344
102000004882 Lipase Human genes 0.000 claims abstract description 344
239000004367 Lipase Substances 0.000 claims abstract description 332
235000019421 lipase Nutrition 0.000 claims abstract description 332
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 144
230000007062 hydrolysis Effects 0.000 claims abstract description 138
108010044467 Isoenzymes Proteins 0.000 claims abstract description 136
239000002253 acid Substances 0.000 claims abstract description 131
150000002148 esters Chemical class 0.000 claims abstract description 130
150000007513 acids Chemical class 0.000 claims abstract description 47
230000000707 stereoselective effect Effects 0.000 claims abstract description 45
238000005809 transesterification reaction Methods 0.000 claims abstract description 30
230000032050 esterification Effects 0.000 claims abstract description 23
238000005886 esterification reaction Methods 0.000 claims abstract description 23
241000222175 Diutina rugosa Species 0.000 claims abstract description 9
230000003301 hydrolyzing effect Effects 0.000 claims abstract description 7
230000000694 effects Effects 0.000 claims description 124
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 111
238000006243 chemical reaction Methods 0.000 claims description 103
DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims description 87
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 87
229960000991 ketoprofen Drugs 0.000 claims description 85
239000000203 mixture Substances 0.000 claims description 81
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 79
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 79
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 79
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 79
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 79
239000005642 Oleic acid Substances 0.000 claims description 78
LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 56
241000222120 Candida <Saccharomycetales> Species 0.000 claims description 49
-1 sulfopropyl derivative of N-acryloyl-2-amino-2-hydroxy-1,3-propanediol Chemical class 0.000 claims description 45
238000001155 isoelectric focusing Methods 0.000 claims description 37
239000003960 organic solvent Substances 0.000 claims description 34
108010093096 Immobilized Enzymes Proteins 0.000 claims description 28
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 28
235000021355 Stearic acid Nutrition 0.000 claims description 26
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 26
239000002904 solvent Substances 0.000 claims description 26
239000008117 stearic acid Substances 0.000 claims description 26
239000004094 surface-active agent Substances 0.000 claims description 22
229920002873 Polyethylenimine Polymers 0.000 claims description 19
239000000654 additive Substances 0.000 claims description 19
150000001413 amino acids Chemical class 0.000 claims description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
230000000996 additive effect Effects 0.000 claims description 15
150000001298 alcohols Chemical class 0.000 claims description 15
239000003638 chemical reducing agent Substances 0.000 claims description 13
150000007524 organic acids Chemical class 0.000 claims description 13
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 12
238000000926 separation method Methods 0.000 claims description 11
230000003100 immobilizing effect Effects 0.000 claims description 10
108090000765 processed proteins & peptides Proteins 0.000 claims description 10
238000000746 purification Methods 0.000 claims description 10
125000001429 N-terminal alpha-amino-acid group Chemical group 0.000 claims description 9
229960004187 indoprofen Drugs 0.000 claims description 9
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical group C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 8
239000004372 Polyvinyl alcohol Substances 0.000 claims description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
239000003456 ion exchange resin Substances 0.000 claims description 8
229920003303 ion-exchange polymer Polymers 0.000 claims description 8
229920002451 polyvinyl alcohol Polymers 0.000 claims description 8
239000000741 silica gel Substances 0.000 claims description 8
229910002027 silica gel Inorganic materials 0.000 claims description 8
AQIHDXGKQHFBNW-UHFFFAOYSA-N 2-(4-hydroxyphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(O)C=C1 AQIHDXGKQHFBNW-UHFFFAOYSA-N 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
RJMIEHBSYVWVIN-LLVKDONJSA-N (2r)-2-[4-(3-oxo-1h-isoindol-2-yl)phenyl]propanoic acid Chemical compound C1=CC([C@H](C(O)=O)C)=CC=C1N1C(=O)C2=CC=CC=C2C1 RJMIEHBSYVWVIN-LLVKDONJSA-N 0.000 claims description 6
235000010265 sodium sulphite Nutrition 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 5
125000004494 ethyl ester group Chemical group 0.000 claims description 5
229940049964 oleate Drugs 0.000 claims description 5
150000003626 triacylglycerols Chemical class 0.000 claims description 5
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 4
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 4
239000003849 aromatic solvent Substances 0.000 claims description 4
229960001680 ibuprofen Drugs 0.000 claims description 4
150000002632 lipids Chemical class 0.000 claims description 4
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical group [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 3
238000004255 ion exchange chromatography Methods 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 3
125000003944 tolyl group Chemical group 0.000 claims description 3
WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 claims description 2
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 2
239000010775 animal oil Substances 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000005456 glyceride group Chemical group 0.000 claims description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
WTTJVINHCBCLGX-NQLNTKRDSA-N methyl linoleate Chemical group CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC WTTJVINHCBCLGX-NQLNTKRDSA-N 0.000 claims description 2
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
229920000642 polymer Polymers 0.000 claims description 2
235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
239000008158 vegetable oil Substances 0.000 claims description 2
235000014113 dietary fatty acids Nutrition 0.000 claims 4
239000000194 fatty acid Substances 0.000 claims 4
229930195729 fatty acid Natural products 0.000 claims 4
229920002307 Dextran Polymers 0.000 claims 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
150000004665 fatty acids Chemical class 0.000 claims 2
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
ZJRZEAWVDDDVPR-UHFFFAOYSA-N 2-(3-benzoylphenyl)propanoic acid 2-[2-(2-methoxyethoxy)ethoxy]ethanol Chemical compound COCCOCCOCCO.OC(=O)C(C)C1=CC(C(=O)C2=CC=CC=C2)=CC=C1 ZJRZEAWVDDDVPR-UHFFFAOYSA-N 0.000 claims 1
ZIZUSDQGFJZAAO-UHFFFAOYSA-N 2-(3-benzoylphenyl)propanoic acid;2-(2-hydroxyethoxy)ethanol Chemical compound OCCOCCO.OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 ZIZUSDQGFJZAAO-UHFFFAOYSA-N 0.000 claims 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
229920000936 Agarose Polymers 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
BCVIOZZGJNOEQS-XKNYDFJKSA-N Ile-Ile Chemical compound CC[C@H](C)[C@H](N)C(=O)N[C@H](C(O)=O)[C@@H](C)CC BCVIOZZGJNOEQS-XKNYDFJKSA-N 0.000 claims 1
DPWFGFQKRVVHHH-UHFFFAOYSA-N OCCOC(=O)C(C)C1=CC(C(=O)C2=CC=CC=C2)=CC=C1 Chemical compound OCCOC(=O)C(C)C1=CC(C(=O)C2=CC=CC=C2)=CC=C1 DPWFGFQKRVVHHH-UHFFFAOYSA-N 0.000 claims 1
125000005907 alkyl ester group Chemical group 0.000 claims 1
125000003275 alpha amino acid group Chemical group 0.000 claims 1
YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical group [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 claims 1
229910000342 sodium bisulfate Inorganic materials 0.000 claims 1
239000012279 sodium borohydride Substances 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 30
238000004519 manufacturing process Methods 0.000 abstract description 13
AQIHDXGKQHFBNW-ZCFIWIBFSA-N (2r)-2-(4-hydroxyphenoxy)propanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=C(O)C=C1 AQIHDXGKQHFBNW-ZCFIWIBFSA-N 0.000 abstract description 7
150000002367 halogens Chemical class 0.000 abstract description 3
229910052736 halogen Inorganic materials 0.000 abstract description 2
229940040461 lipase Drugs 0.000 description 271
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 110
229940088598 enzyme Drugs 0.000 description 104
239000000872 buffer Substances 0.000 description 88
229920006130 high-performance polyamide Polymers 0.000 description 79
235000021313 oleic acid Nutrition 0.000 description 78
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 64
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
239000000243 solution Substances 0.000 description 52
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
238000004128 high performance liquid chromatography Methods 0.000 description 36
102000004169 proteins and genes Human genes 0.000 description 36
108090000623 proteins and genes Proteins 0.000 description 36
239000011541 reaction mixture Substances 0.000 description 35
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
235000018102 proteins Nutrition 0.000 description 32
239000000499 gel Substances 0.000 description 28
239000011324 bead Substances 0.000 description 27
239000008363 phosphate buffer Substances 0.000 description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
239000008367 deionised water Substances 0.000 description 22
229910021641 deionized water Inorganic materials 0.000 description 22
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
239000001913 cellulose Substances 0.000 description 21
229920002678 cellulose Polymers 0.000 description 21
229920001429 chelating resin Polymers 0.000 description 21
239000000758 substrate Substances 0.000 description 20
LRDIEHDJWYRVPT-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 LRDIEHDJWYRVPT-UHFFFAOYSA-N 0.000 description 19
238000002474 experimental method Methods 0.000 description 19
150000004702 methyl esters Chemical class 0.000 description 19
239000012071 phase Substances 0.000 description 19
LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 18
229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 18
235000019837 monoammonium phosphate Nutrition 0.000 description 18
239000003921 oil Substances 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
235000019198 oils Nutrition 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000004458 analytical method Methods 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
238000001514 detection method Methods 0.000 description 12
238000010828 elution Methods 0.000 description 12
239000004006 olive oil Substances 0.000 description 12
235000008390 olive oil Nutrition 0.000 description 12
230000003287 optical effect Effects 0.000 description 12
239000000047 product Substances 0.000 description 12
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 11
239000005695 Ammonium acetate Substances 0.000 description 11
235000019257 ammonium acetate Nutrition 0.000 description 11
229940043376 ammonium acetate Drugs 0.000 description 11
239000011942 biocatalyst Substances 0.000 description 11
230000002051 biphasic effect Effects 0.000 description 11
238000004587 chromatography analysis Methods 0.000 description 11
235000001014 amino acid Nutrition 0.000 description 10
229940024606 amino acid Drugs 0.000 description 10
230000007071 enzymatic hydrolysis Effects 0.000 description 10
238000006047 enzymatic hydrolysis reaction Methods 0.000 description 10
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
KAPCRJOPWXUMSQ-UHFFFAOYSA-N [2,2-bis[3-(aziridin-1-yl)propanoyloxymethyl]-3-hydroxypropyl] 3-(aziridin-1-yl)propanoate Chemical compound C1CN1CCC(=O)OCC(COC(=O)CCN1CC1)(CO)COC(=O)CCN1CC1 KAPCRJOPWXUMSQ-UHFFFAOYSA-N 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
238000002955 isolation Methods 0.000 description 9
229920000136 polysorbate Polymers 0.000 description 9
230000035484 reaction time Effects 0.000 description 9
239000007787 solid Substances 0.000 description 9
USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 description 8
239000004254 Ammonium phosphate Substances 0.000 description 8
108091003079 Bovine Serum Albumin Proteins 0.000 description 8
150000001408 amides Chemical class 0.000 description 8
229910000148 ammonium phosphate Inorganic materials 0.000 description 8
235000019289 ammonium phosphates Nutrition 0.000 description 8
229940098773 bovine serum albumin Drugs 0.000 description 8
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
238000000605 extraction Methods 0.000 description 8
239000000463 material Substances 0.000 description 8
229920005989 resin Polymers 0.000 description 8
239000011347 resin Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
108090000371 Esterases Proteins 0.000 description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 7
239000008346 aqueous phase Substances 0.000 description 7
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 7
239000002953 phosphate buffered saline Substances 0.000 description 7
239000000523 sample Substances 0.000 description 7
238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 7
239000006228 supernatant Substances 0.000 description 7
GHCZTIFQWKKGSB-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;phosphoric acid Chemical compound OP(O)(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O GHCZTIFQWKKGSB-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
102000012440 Acetylcholinesterase Human genes 0.000 description 6
108010022752 Acetylcholinesterase Proteins 0.000 description 6
SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 6
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
229940022698 acetylcholinesterase Drugs 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 6
239000004913 cyclooctene Substances 0.000 description 6
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 6
239000003480 eluent Substances 0.000 description 6
230000002255 enzymatic effect Effects 0.000 description 6
238000006911 enzymatic reaction Methods 0.000 description 6
210000004185 liver Anatomy 0.000 description 6
229910000403 monosodium phosphate Inorganic materials 0.000 description 6
235000019799 monosodium phosphate Nutrition 0.000 description 6
150000002888 oleic acid derivatives Chemical class 0.000 description 6
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 6
229920000053 polysorbate 80 Polymers 0.000 description 6
239000011734 sodium Substances 0.000 description 6
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 6
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 6
238000003756 stirring Methods 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 5
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 5
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 5
235000019626 lipase activity Nutrition 0.000 description 5
239000011777 magnesium Substances 0.000 description 5
239000002480 mineral oil Substances 0.000 description 5
235000010446 mineral oil Nutrition 0.000 description 5
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 5
239000000126 substance Substances 0.000 description 5
LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 description 4
229920005654 Sephadex Polymers 0.000 description 4
239000012507 Sephadex™ Substances 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000003556 assay Methods 0.000 description 4
238000005119 centrifugation Methods 0.000 description 4
230000008859 change Effects 0.000 description 4
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
229960003067 cystine Drugs 0.000 description 4
230000003247 decreasing effect Effects 0.000 description 4
238000010790 dilution Methods 0.000 description 4
239000012895 dilution Substances 0.000 description 4
238000005342 ion exchange Methods 0.000 description 4
235000005985 organic acids Nutrition 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
230000020477 pH reduction Effects 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
238000012163 sequencing technique Methods 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
238000005406 washing Methods 0.000 description 4
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 4
CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 description 3
HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
101710098554 Lipase B Proteins 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 3
229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
241000282898 Sus scrofa Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
241000179532 [Candida] cylindracea Species 0.000 description 3
238000002835 absorbance Methods 0.000 description 3
239000008351 acetate buffer Substances 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
239000012062 aqueous buffer Substances 0.000 description 3
OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 3
230000008901 benefit Effects 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000011161 development Methods 0.000 description 3
229940079919 digestives enzyme preparation Drugs 0.000 description 3
238000009472 formulation Methods 0.000 description 3
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 3
239000012510 hollow fiber Substances 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
YNZYUHPFNYBBFF-UHFFFAOYSA-N methyl 2-[4-(2-methylpropyl)phenyl]propanoate Chemical compound COC(=O)C(C)C1=CC=C(CC(C)C)C=C1 YNZYUHPFNYBBFF-UHFFFAOYSA-N 0.000 description 3
DZIQUZJSNSZOCH-UHFFFAOYSA-N methyl 2-phenylpropanoate Chemical compound COC(=O)C(C)C1=CC=CC=C1 DZIQUZJSNSZOCH-UHFFFAOYSA-N 0.000 description 3
229910000402 monopotassium phosphate Inorganic materials 0.000 description 3
235000019796 monopotassium phosphate Nutrition 0.000 description 3
238000005457 optimization Methods 0.000 description 3
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
230000004044 response Effects 0.000 description 3
230000000717 retained effect Effects 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000007858 starting material Substances 0.000 description 3
229950011008 tetrachloroethylene Drugs 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 2
UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
HGSAZSYSPVGGRS-UHFFFAOYSA-N 2-(3-benzoylphenyl)propanoic acid;ethane-1,2-diol Chemical compound OCCO.OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 HGSAZSYSPVGGRS-UHFFFAOYSA-N 0.000 description 2
CMWTZPSULFXXJA-UHFFFAOYSA-N 2-(6-methoxy-2-naphthalenyl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 2
BLXVTZPGEOGTGG-UHFFFAOYSA-N 2-[2-(4-nonylphenoxy)ethoxy]ethanol Chemical compound CCCCCCCCCC1=CC=C(OCCOCCO)C=C1 BLXVTZPGEOGTGG-UHFFFAOYSA-N 0.000 description 2
JKXYOQDLERSFPT-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-octadecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO JKXYOQDLERSFPT-UHFFFAOYSA-N 0.000 description 2
IEQAICDLOKRSRL-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO IEQAICDLOKRSRL-UHFFFAOYSA-N 0.000 description 2
QDJOFGCFCRWUQE-UHFFFAOYSA-N 2-chloroethyl 2-(3-benzoylphenyl)propanoate Chemical compound ClCCOC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 QDJOFGCFCRWUQE-UHFFFAOYSA-N 0.000 description 2
DFVOXRAAHOJJBN-UHFFFAOYSA-N 6-methylhept-1-ene Chemical compound CC(C)CCCC=C DFVOXRAAHOJJBN-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 2
OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
108020004511 Recombinant DNA Proteins 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
241000251733 Tetronarce californica Species 0.000 description 2
QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 2
244000025271 Umbellularia californica Species 0.000 description 2
DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
235000020661 alpha-linolenic acid Nutrition 0.000 description 2
238000013459 approach Methods 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
239000012455 biphasic mixture Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
230000009089 cytolysis Effects 0.000 description 2
HEFNNWSXXWATRW-JTQLQIEISA-N dexibuprofen Chemical compound CC(C)CC1=CC=C([C@H](C)C(O)=O)C=C1 HEFNNWSXXWATRW-JTQLQIEISA-N 0.000 description 2
238000010586 diagram Methods 0.000 description 2
238000000502 dialysis Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
238000010931 ester hydrolysis Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
238000004108 freeze drying Methods 0.000 description 2
KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical compound CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 description 2
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 2
VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
230000006872 improvement Effects 0.000 description 2
238000011534 incubation Methods 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
235000020778 linoleic acid Nutrition 0.000 description 2
KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 2
229960004488 linolenic acid Drugs 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000002609 medium Substances 0.000 description 2
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 2
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
150000002889 oleic acids Chemical class 0.000 description 2
230000036961 partial effect Effects 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 2
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
229920002401 polyacrylamide Polymers 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
238000005070 sampling Methods 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000012064 sodium phosphate buffer Substances 0.000 description 2
210000002435 tendon Anatomy 0.000 description 2
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
150000003738 xylenes Chemical class 0.000 description 2
NNJPGOLRFBJNIW-HNNXBMFYSA-N (-)-demecolcine Chemical compound C1=C(OC)C(=O)C=C2[C@@H](NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-HNNXBMFYSA-N 0.000 description 1
QZNNVYOVQUKYSC-JEDNCBNOSA-N (2s)-2-amino-3-(1h-imidazol-5-yl)propanoic acid;hydron;chloride Chemical compound Cl.OC(=O)[C@@H](N)CC1=CN=CN1 QZNNVYOVQUKYSC-JEDNCBNOSA-N 0.000 description 1
IHAIQFIIVUZFHC-IPIKRLCPSA-N (2s)-2-amino-3-phenylpropanoic acid;(2s)-pyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1.OC(=O)[C@@H](N)CC1=CC=CC=C1 IHAIQFIIVUZFHC-IPIKRLCPSA-N 0.000 description 1
YUXKOWPNKJSTPQ-AXWWPMSFSA-N (2s,3r)-2-amino-3-hydroxybutanoic acid;(2s)-2-amino-3-hydroxypropanoic acid Chemical compound OC[C@H](N)C(O)=O.C[C@@H](O)[C@H](N)C(O)=O YUXKOWPNKJSTPQ-AXWWPMSFSA-N 0.000 description 1
OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
HBOQXIRUPVQLKX-BBWANDEASA-N 1,2,3-trilinoleoylglycerol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COC(=O)CCCCCCC\C=C/C\C=C/CCCCC HBOQXIRUPVQLKX-BBWANDEASA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
MQGBAQLIFKSMEM-MAZCIEHSSA-N 1,2-dilinoleoylglycerol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC MQGBAQLIFKSMEM-MAZCIEHSSA-N 0.000 description 1
FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 1
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
MFSJSVNVUDQHLV-UHFFFAOYSA-N 2-(3-benzoylphenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1.OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 MFSJSVNVUDQHLV-UHFFFAOYSA-N 0.000 description 1
AMCMPYSRJBOXBL-UHFFFAOYSA-N 2-(4-hydroxyphenoxy)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(O)C=C1 AMCMPYSRJBOXBL-UHFFFAOYSA-N 0.000 description 1
MGYUQZIGNZFZJS-KTKRTIGZSA-N 2-[2-[(z)-octadec-9-enoxy]ethoxy]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCOCCO MGYUQZIGNZFZJS-KTKRTIGZSA-N 0.000 description 1
HNUQMTZUNUBOLQ-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-(2-octadecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO HNUQMTZUNUBOLQ-UHFFFAOYSA-N 0.000 description 1
VRVIDSRWPUGFBU-UHFFFAOYSA-N 2-chloro-1,1,1-trifluoropropane Chemical compound CC(Cl)C(F)(F)F VRVIDSRWPUGFBU-UHFFFAOYSA-N 0.000 description 1
MYCXCBCDXVFXNE-UHFFFAOYSA-N 2-chloro-2-methylpropanoic acid Chemical class CC(C)(Cl)C(O)=O MYCXCBCDXVFXNE-UHFFFAOYSA-N 0.000 description 1
TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
ABOOPXYCKNFDNJ-UHFFFAOYSA-N 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-UHFFFAOYSA-N 0.000 description 1
AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
208000002109 Argyria Diseases 0.000 description 1
DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
WVSAFJPKTISBIL-KVVVOXFISA-N CCCCCC.CCCCCCCC\C=C/CCCCCCCC(O)=O Chemical compound CCCCCC.CCCCCCCC\C=C/CCCCCCCC(O)=O WVSAFJPKTISBIL-KVVVOXFISA-N 0.000 description 1
101100310222 Caenorhabditis briggsae she-1 gene Proteins 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
240000004385 Centaurea cyanus Species 0.000 description 1
235000005940 Centaurea cyanus Nutrition 0.000 description 1
229920002101 Chitin Polymers 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
241000277305 Electrophorus electricus Species 0.000 description 1
101000635852 Equus caballus Myoglobin Proteins 0.000 description 1
SPJOZZSIXXJYBT-UHFFFAOYSA-N Fenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=CC=C1 SPJOZZSIXXJYBT-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000976416 Isatis tinctoria subsp. canescens Species 0.000 description 1
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
102000008192 Lactoglobulins Human genes 0.000 description 1
108010060630 Lactoglobulins Proteins 0.000 description 1
239000005639 Lauric acid Substances 0.000 description 1
102000004856 Lectins Human genes 0.000 description 1
108090001090 Lectins Proteins 0.000 description 1
ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
235000021353 Lignoceric acid Nutrition 0.000 description 1
CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 1
101710084376 Lipase 3 Proteins 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
235000021360 Myristic acid Nutrition 0.000 description 1
TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
101150019103 NAT2 gene Proteins 0.000 description 1
239000002033 PVDF binder Substances 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
108050006759 Pancreatic lipases Proteins 0.000 description 1
102000019280 Pancreatic lipases Human genes 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920001213 Polysorbate 20 Polymers 0.000 description 1
229920001214 Polysorbate 60 Polymers 0.000 description 1
241000235403 Rhizomucor miehei Species 0.000 description 1
239000012506 Sephacryl® Substances 0.000 description 1
238000010266 Sephadex chromatography Methods 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
239000004473 Threonine Substances 0.000 description 1
101710162629 Trypsin inhibitor Proteins 0.000 description 1
229940122618 Trypsin inhibitor Drugs 0.000 description 1
102000018690 Trypsinogen Human genes 0.000 description 1
108010027252 Trypsinogen Proteins 0.000 description 1
KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Chemical compound CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
LWZFANDGMFTDAV-BURFUSLBSA-N [(2r)-2-[(2r,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O LWZFANDGMFTDAV-BURFUSLBSA-N 0.000 description 1
YLNSNVGRSIOCEU-ZCFIWIBFSA-N [(2r)-oxiran-2-yl]methyl butanoate Chemical compound CCCC(=O)OC[C@H]1CO1 YLNSNVGRSIOCEU-ZCFIWIBFSA-N 0.000 description 1
CDXSJGDDABYYJV-UHFFFAOYSA-N acetic acid;ethanol Chemical compound CCO.CC(O)=O CDXSJGDDABYYJV-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000009471 action Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
235000004279 alanine Nutrition 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
229940111131 antiinflammatory and antirheumatic product propionic acid derivative Drugs 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
239000002635 aromatic organic solvent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
229960001230 asparagine Drugs 0.000 description 1
235000009582 asparagine Nutrition 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
238000011914 asymmetric synthesis Methods 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
230000008033 biological extinction Effects 0.000 description 1
239000012888 bovine serum Substances 0.000 description 1
230000003139 buffering effect Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
230000007073 chemical hydrolysis Effects 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
239000007979 citrate buffer Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000013068 control sample Substances 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000010612 desalination reaction Methods 0.000 description 1
239000003599 detergent Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001962 electrophoresis Methods 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
FMMOOAYVCKXGMF-MURFETPASA-N ethyl linoleate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC FMMOOAYVCKXGMF-MURFETPASA-N 0.000 description 1
229940071106 ethylenediaminetetraacetate Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229930195712 glutamate Natural products 0.000 description 1
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
UHUSDOQQWJGJQS-UHFFFAOYSA-N glycerol 1,2-dioctadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCCCCCCCC UHUSDOQQWJGJQS-UHFFFAOYSA-N 0.000 description 1
RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 1
150000002314 glycerols Chemical class 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
239000000017 hydrogel Substances 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
239000003622 immobilized catalyst Substances 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
229960000310 isoleucine Drugs 0.000 description 1
239000002523 lectin Substances 0.000 description 1
FMMOOAYVCKXGMF-UHFFFAOYSA-N linoleic acid ethyl ester Natural products CCCCCC=CCC=CCCCCCCCC(=O)OCC FMMOOAYVCKXGMF-UHFFFAOYSA-N 0.000 description 1
HBOQXIRUPVQLKX-UHFFFAOYSA-N linoleic acid triglyceride Natural products CCCCCC=CCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC HBOQXIRUPVQLKX-UHFFFAOYSA-N 0.000 description 1
150000002634 lipophilic molecules Chemical class 0.000 description 1
238000011068 loading method Methods 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000012528 membrane Substances 0.000 description 1
238000005374 membrane filtration Methods 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
UUYSCNGPNOYZMC-UHFFFAOYSA-N methyl 2-(4-hydroxyphenoxy)propanoate Chemical compound COC(=O)C(C)OC1=CC=C(O)C=C1 UUYSCNGPNOYZMC-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
CEQFOVLGLXCDCX-WUKNDPDISA-N methyl red Chemical compound C1=CC(N(C)C)=CC=C1\N=N\C1=CC=CC=C1C(O)=O CEQFOVLGLXCDCX-WUKNDPDISA-N 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
244000005700 microbiome Species 0.000 description 1
230000003228 microsomal effect Effects 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
229940074096 monoolein Drugs 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
229960002009 naproxen Drugs 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
239000006225 natural substrate Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
235000014571 nuts Nutrition 0.000 description 1
BGMYDZVCAOVIPM-UHFFFAOYSA-N octyl 2-chloropropanoate Chemical compound CCCCCCCCOC(=O)C(C)Cl BGMYDZVCAOVIPM-UHFFFAOYSA-N 0.000 description 1
239000011368 organic material Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000000963 oxybis(methylene) group Chemical group [H]C([H])(*)OC([H])([H])* 0.000 description 1
239000006174 pH buffer Substances 0.000 description 1
229940116369 pancreatic lipase Drugs 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
239000012450 pharmaceutical intermediate Substances 0.000 description 1
229920001983 poloxamer Polymers 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
238000002264 polyacrylamide gel electrophoresis Methods 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229920002981 polyvinylidene fluoride Polymers 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
150000005599 propionic acid derivatives Chemical class 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
235000004252 protein component Nutrition 0.000 description 1
239000012460 protein solution Substances 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000000700 radioactive tracer Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000013074 reference sample Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000007974 sodium acetate buffer Substances 0.000 description 1
SIGUVTURIMRFDD-UHFFFAOYSA-M sodium dioxidophosphanium Chemical compound [Na+].[O-][PH2]=O SIGUVTURIMRFDD-UHFFFAOYSA-M 0.000 description 1
CSMWJXBSXGUPGY-UHFFFAOYSA-L sodium dithionate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)S([O-])(=O)=O CSMWJXBSXGUPGY-UHFFFAOYSA-L 0.000 description 1
229940075931 sodium dithionate Drugs 0.000 description 1
229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
235000011008 sodium phosphates Nutrition 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
235000011067 sorbitan monolaureate Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
QZZGJDVWLFXDLK-UHFFFAOYSA-N tetracosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(O)=O QZZGJDVWLFXDLK-UHFFFAOYSA-N 0.000 description 1
TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
DPUOLQHDNGRHBS-MDZDMXLPSA-N trans-Brassidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-MDZDMXLPSA-N 0.000 description 1
229940081852 trilinolein Drugs 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
239000002753 trypsin inhibitor Substances 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
238000000108 ultra-filtration Methods 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
239000003981 vehicle Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6409—Fatty acids
- C12P7/6418—Fatty acids by hydrolysis of fatty acid esters
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
- C12N9/18—Carboxylic ester hydrolases (3.1.1)
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/005—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of carboxylic acid groups in the enantiomers or the inverse reaction
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/62—Carboxylic acid esters
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6454—Glycerides by esterification
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6458—Glycerides by transesterification, e.g. interesterification, ester interchange, alcoholysis or acidolysis
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6472—Glycerides containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Bioinformatics & Cheminformatics (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
General Engineering & Computer Science (AREA)
Microbiology (AREA)
Biochemistry (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
Analytical Chemistry (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Biomedical Technology (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Enzymes And Modification Thereof (AREA)
Immobilizing And Processing Of Enzymes And Microorganisms (AREA)

HU904853A 1989-06-05 1990-06-01 Process for producing and applying enzymes HUT61050A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/361,049 US5108916A (en)	1989-06-05	1989-06-05	Process for stereoselectively hydrolyzing, transesterifying or esterifying with immobilized isozyme of lipase from candida rugosa

Publications (2)

Publication Number	Publication Date
HU904853D0 HU904853D0 (en)	1992-02-28
HUT61050A true HUT61050A (en)	1992-11-30

Family

ID=23420444

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU904853A HUT61050A (en)	1989-06-05	1990-06-01	Process for producing and applying enzymes

Country Status (12)

Country	Link
US (1)	US5108916A (de)
EP (1)	EP0407033A3 (de)
JP (1)	JPH05500452A (de)
KR (1)	KR920701457A (de)
AU (1)	AU637113B2 (de)
CA (1)	CA2057007A1 (de)
HU (1)	HUT61050A (de)
IL (1)	IL94545A (de)
NZ (1)	NZ233849A (de)
PT (1)	PT94253A (de)
WO (1)	WO1990015146A1 (de)
ZA (1)	ZA904121B (de)

Families Citing this family (53)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5342780A (en) *	1990-01-26	1994-08-30	University Of New Mexico	Methods of enzymatically separating stereoisomers of a racemic mixture of a reactive ester
IT1249777B (it)	1990-05-17	1995-03-18	Zambon Spa	Processo per la preparazione di intermedi per la sintesi del diltiazem
AT398081B (de) *	1991-04-29	1994-09-26	Chemie Linz Gmbh	Verfahren zur enzymatischen hydrolyse eines carbonsäurederivates
US5262313A (en) *	1991-06-14	1993-11-16	Andcare, Inc.	Carrageeman-immobilized esterase
GB9118149D0 (en) *	1991-08-22	1991-10-09	Enzymatix Ltd	Araylalkanoic acid resolution
GB9118150D0 (en) *	1991-08-22	1991-10-09	Enzymatix Ltd	Arylalkanoic acid resolution
AT398310B (de) *	1991-08-30	1994-11-25	Chemie Linz Gmbh	Immobilisierte lipase, verfahren zu ihrer herstellung sowie verfahren zur erhöhung der enantioselektivität einer candida lipase bei der veresterung chiraler alkohole
EP0536671B1 (de) *	1991-10-07	1996-03-06	Hoechst Aktiengesellschaft	Carbonsäureester-Schutzgruppen, ein Verfahren zu ihrer Herstellung, ihre Kopplung an eine funktionelle Gruppe sowie ihre Verwendung
US5541080A (en) *	1991-11-01	1996-07-30	Wisconsin Alumni Research Fdn.	Method for preparing L-alpha-amino acids
US5219731A (en) *	1991-11-01	1993-06-15	Wisconsin Alumni Research Foundation	Method for preparing optically-active amino acid derivatives
EP0567661A1 (de) *	1992-04-25	1993-11-03	Societe Des Produits Nestle S.A.	Modifizierte Lipase, Verfahren zur Modifizierung und Verwendungen
EP0567662B1 (de) *	1992-04-25	1997-03-05	Societe Des Produits Nestle S.A.	Verfahren zur Aromatisierung von Milchschokolade
ES2050067B1 (es) *	1992-06-08	1994-12-16	Menarini Lab	Proceso para la produccion de acido s-(+)-2-(3-benzoilfenil) propionico por transesterificacion enantioselectiva con un alcohol bifuncional catalizada enzimaticamente en medio organico.
ES2046950B1 (es) *	1992-06-08	1994-10-01	Menarini Lab	Proceso para la produccion de acido s-(+)-2-(3-benzoilfenil)propionico por hidrolisis enantioselectiva catalizada enzimaticamente.
ES2048653B1 (es) *	1992-06-08	1994-12-16	Menarini Lab	Proceso para la produccion de acido s-(+)-2-(3-benzoilfenil) propionico por transesterificacion enantioselectiva catalizada enzimaticamente en un disolvente organico.
ES2050068B1 (es) *	1992-07-03	1994-12-16	Consejo Superior Investigacion	Procedimiento para la purificacion de dos isoenzimas lipasa de candida rugosa.
US5912164A (en) *	1993-03-03	1999-06-15	Laboratorios Menarini S.A.	Stereoselective hydrolysis of chiral carboxylic acid esters using esterase from ophiostoma or ceratocystis
GB9304256D0 (en) *	1993-03-03	1993-04-21	Chiros Ltd	Arylalkanoic acid resolution
GB9304351D0 (en) *	1993-03-03	1993-04-21	Chiros Ltd	Arylalkanoic acid resolution and microorganisms for use therein
US5457051A (en) *	1993-03-09	1995-10-10	Sepracor, Inc.	Enantioselective hydrolysis of ketoprofen esters by beauveria bassiana and enzymes derived therefrom
AT400036B (de) *	1993-10-15	1995-09-25	Pittner Fritz	Mit enzym markierte probe oder testsubstanz
AT401385B (de) *	1994-03-30	1996-08-26	Chemie Linz Gmbh	Enzymatische racematspaltung asymmetrischer alkohole mittels vinylestern mehrbasiger carbonsäuren
DE4414273A1 (de) *	1994-04-23	1995-10-26	Chemie Linz Deutschland	Enzymatische Racematspaltung asymmetrischer Alkohole mittels Vinylestern mehrbasiger Carbonsäuren
FR2724184B1 (fr) *	1994-09-05	1997-01-03	Rhone Poulenc Chimie	Procede de resolution d'un melange d'alcools stereoisomeres
US5580783A (en) *	1994-10-12	1996-12-03	E. I. Du Pont De Nemours And Company	Enzymatic process for the preparation of chiral α-tertiary carboxylic acid esters
US6022977A (en) *	1997-03-26	2000-02-08	Dupont Pharmaceuticals Company	Dynamic resolution of isoxazoline thioesters to isoxazoline carboxylic acids
US6461858B1 (en)	1998-01-26	2002-10-08	Pharm-Eco Laboratories, Inc.	Enzyme activated supports for enantiomeric separations
EP1067196B1 (de) *	1998-03-31	2009-02-18	Takara Bio Inc.	Verfahren zur herstellung von lysosphingolipiden
CN1065917C (zh) *	1998-10-12	2001-05-16	华东理工大学	外消旋酮基布洛芬的酶法拆分工艺
JP2000154200A (ja) *	1998-11-20	2000-06-06	Kanegafuchi Chem Ind Co Ltd	化合物の固定化方法
DE19901925A1 (de) *	1999-01-19	2000-07-27	Aventis Res & Tech Gmbh & Co	Verfahren zur Trennung optischer Isomerer durch simultane Durchführung einer enzymatischen Reaktion und einer chromatographischen Trennung
GB9907082D0 (en) *	1999-03-26	1999-05-19	Chirotech Technology Ltd	The preparation of carboxylic acid derivatives
DE19931847A1 (de) *	1999-07-09	2001-01-11	Basf Ag	Immobilisierte Lipase
IT1315212B1 (it) *	1999-07-26	2003-02-03	Consiglio Nazionale Ricerche	Impiego di ortoesteri per la sintesi di acidi chirali in processi diesterificazione irreversibili biocatalizzati.
US20020061566A1 (en) *	2000-03-20	2002-05-23	Eirich L. Dudley	Biooxidation capabilities of candida sp
KR100868619B1 (ko) *	2001-03-07	2008-11-13	다이이찌 세이야꾸 가부시기가이샤	광학활성인 프로폭시아닐린 유도체의 제조방법
US20030054509A1 (en) *	2001-04-06	2003-03-20	Archer-Daniels-Midland Company	Method for producing fats or oils
CN100413972C (zh)	2001-09-25	2008-08-27	弗·哈夫曼-拉罗切有限公司	制备取代的2-氨基-3-(2-氨基-苯硫基)-丙酸的酶催化方法
KR100433633B1 (ko) *	2002-04-18	2004-05-31	학교법인 포항공과대학교	무용매 이상계 시스템을 이용한 효소적 광학분할 방법
CA3007908A1 (en)	2003-03-07	2005-04-14	Dsm Ip Assets B.V.	Hydrolases, nucleic acids encoding them and methods for making and using them
CA2532672A1 (en)	2003-07-16	2005-02-03	Archer-Daniels-Midland Company	Method for producing fats or oils
MY134420A (en) *	2004-02-18	2007-12-31	Univ Putra Malaysia Upm	Enantioselective immobilized lipase
DE102004019472A1 (de) *	2004-04-22	2005-11-17	Bayer Healthcare Ag	Phenylacetamide
KR100657212B1 (ko) *	2004-04-29	2006-12-14	엔자이텍 주식회사	라세믹 에스테르로부터 광학활성 에스테르 유도체와 이의 산의 제조 방법
EP1987142A4 (de)	2006-02-02	2009-07-15	Verenium Corp	Esterasen und damit zusammenhängende nukleinsäuren und verfahren
US8252564B2 (en)	2006-04-06	2012-08-28	Lg Chem, Ltd.	Burkholderia multivorans strain and methods of using same
UA97127C2 (uk) *	2006-12-06	2012-01-10	Бандж Ойлз, Инк.	Спосіб безперервної ферментативної обробки композиції, що містить ліпід, та система для його здійснення
US8268305B1 (en)	2011-09-23	2012-09-18	Bio-Cat, Inc.	Method and compositions to reduce serum levels of triacylglycerides in human beings using a fungal lipase
DK4242305T3 (en) *	2014-05-20	2026-03-23	Bunge Loders Croklaan B V	Process for immobilization of a lipase
CN106518969B (zh) *	2016-11-15	2019-03-15	郑州大学第一附属医院	与脂肪酶靶向结合的肽配基序列及其应用
CN109486897A (zh) *	2018-12-04	2019-03-19	湖南理工学院	一种立体选择性酶催化水解拆分2-苯基丙酸对映体的方法
SG10201914033YA (en) *	2019-12-31	2021-07-29	Wilmar International Ltd	Polypeptides with Lipase Activity and Uses Thereof
CN121343960B (zh) *	2025-12-19	2026-03-27	内蒙古科为博生物科技有限公司	一种碱性脂肪酶突变体及其制备方法、应用和产品

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB976415A (en) *	1961-09-25	1964-11-25	Meito Sangyo Kk	High-activity lipase and method of preparation thereof
DE3163939D1 (en) *	1980-03-08	1984-07-12	Fuji Oil Co Ltd	Method for enzymatic interesterification of lipid and enzyme used therein
US4650755A (en) *	1983-02-10	1987-03-17	Purification Engineering, Inc.	Immobilizing microbial cells with polyfunctional aziridines
DK402583D0 (da) *	1983-09-05	1983-09-05	Novo Industri As	Fremgangsmade til fremstilling af et immobiliseret lipasepraeparat og anvendelse deraf
US4601987A (en) *	1985-02-27	1986-07-22	Massachusetts Institute Of Technology	Enzymatic production of optical isomers of 2-halopropionic acids
US4668628A (en) *	1985-04-01	1987-05-26	Stauffer Chemical Company	Resolution of racemic mixtures of aliphatic acid esters
DE3532026A1 (de) *	1985-09-09	1987-03-19	Hoechst Ag	Verfahren zur herstellung optisch aktiver (alpha)-phenoxypropionsaeure und deren derivate
JPH066058B2 (ja) *	1985-12-07	1994-01-26	不二製油株式会社	酵素剤の製造法
DK620486A (da) *	1985-12-20	1987-06-21	Wisconsin Alumni Res Found	Fremgangsmaade til fremstilling af eddikesyrederivater
US4897357A (en) *	1985-12-31	1990-01-30	Ethyl Corporation	(S) α-cyano-3-phenoxy-benzyl acetate
JPS6460392A (en) *	1987-09-01	1989-03-07	Itoham Foods Inc	Modification of fat and oil
US4923810A (en) *	1988-08-24	1990-05-08	Genzyme Corporation	Resolution of glycidyl esters to high enantiomeric excess

1989
- 1989-06-05 US US07/361,049 patent/US5108916A/en not_active Expired - Fee Related
1990
- 1990-05-29 NZ NZ233849A patent/NZ233849A/en unknown
- 1990-05-29 IL IL9454590A patent/IL94545A/en not_active IP Right Cessation
- 1990-05-29 ZA ZA904121A patent/ZA904121B/xx unknown
- 1990-06-01 HU HU904853A patent/HUT61050A/hu unknown
- 1990-06-01 KR KR1019910701772A patent/KR920701457A/ko not_active Withdrawn
- 1990-06-01 WO PCT/US1990/002990 patent/WO1990015146A1/en not_active Ceased
- 1990-06-01 AU AU58242/90A patent/AU637113B2/en not_active Ceased
- 1990-06-01 CA CA002057007A patent/CA2057007A1/en not_active Abandoned
- 1990-06-01 JP JP2508806A patent/JPH05500452A/ja active Pending
- 1990-06-04 PT PT94253A patent/PT94253A/pt not_active Application Discontinuation
- 1990-06-05 EP EP19900306098 patent/EP0407033A3/en not_active Withdrawn

Also Published As

Publication number	Publication date
ZA904121B (en)	1991-05-29
AU5824290A (en)	1991-01-07
HU904853D0 (en)	1992-02-28
CA2057007A1 (en)	1990-12-06
WO1990015146A1 (en)	1990-12-13
JPH05500452A (ja)	1993-02-04
EP0407033A3 (en)	1991-04-03
US5108916A (en)	1992-04-28
AU637113B2 (en)	1993-05-20
IL94545A (en)	1994-05-30
EP0407033A2 (de)	1991-01-09
NZ233849A (en)	1992-06-25
PT94253A (pt)	1991-02-08
KR920701457A (ko)	1992-08-11

Legal Events

Date	Code	Title	Description
1994-03-28	DFD9	Temporary protection cancelled due to non-payment of fee

Publication	Publication Date	Title
HUT61050A (en)	1992-11-30	Process for producing and applying enzymes
Häring et al.	1999	Cross-linked enzyme crystals
Palomo et al.	2002	Modulation of the enantioselectivity of lipases via controlled immobilization and medium engineering: hydrolytic resolution of mandelic acid esters
Lam et al.	1988	Enzymes in organic synthesis. 42. Investigation of the effects of the isozymal composition of pig liver esterase on its stereoselectivity in preparative-scale ester hydrolysis of asymmetric synthetic value
Basri et al.	1996	Immobilization of lipase from Candida rugosa on synthetic polymer beads for use in the synthesis of fatty esters
Secundo et al.	2004	Activity and enantioselectivity of wildtype and lid mutated Candida rugosa lipase isoform 1 in organic solvents
EP0305901A2 (de)	1989-03-08	Verfahren zur Umesterung von Ölen und Fetten in Anwesenheit einer Fettsäure, eines Fettsäureesters oder eines anderen Öls oder Fettes mittels einer alkalischen hoch-molekularen Lipase
Reslow et al.	1992	Modification of the microenvironment of enzymes in organic solvents. Substitution of water by polar solvents
JPS5991895A (ja)	1984-05-26	非天然セフアロスポリンの製造方法
CA2000143A1 (en)	1990-04-04	Production of monoglycerides by enzymatic transesterification
de Morais Júnior et al.	2018	Influence of different immobilization techniques to improve the enantioselectivity of lipase from Geotrichum candidum applied on the resolution of mandelic acid
Gais et al.	2001	Activation of pig liver esterase in organic media with organic polymers. Application to the enantioselective acylation of racemic functionalized secondary alcohols
Yokoigawa et al.	1994	Enantioselective synthesis of N-acetyl-L-methionine with aminoacylase in organic solvent
Ryu et al.	1987	Semisynthetic β-lactam antibiotics synthesizing enzyme from Acetobacter turbidans: purification and properties
Nakamoto et al.	1979	Amino acid esterification by α-chymotrypsin immobilized in spiropyran membrane
US20240425829A1 (en)	2024-12-26	Enzyme agent for transesterification, including lipase as active ingredient
US4042461A (en)	1977-08-16	Method for purifying cholesterol esterase
Scollar et al.	1985	Preparative resolution of d, l‐threonine catalyzed by immobilized phosphatase
Martinek et al.	1981	Enzyme catalysis in organic synthesis
Lin et al.	1993	Novel acyl donors for enzyme-catalyzed transacylation reactions
JP2891023B2 (ja)	1999-05-17	ランチオニン含有物の製造方法
EP0494881B1 (de)	1994-05-04	Interesterifikation von phospholipiden
JP2000078971A (ja)	2000-03-21	Ｄ−、ｌ−アミノ酸エステルよりオリゴペプチドを合成する新規酵素およびこれを生産する微生物
JP5619400B2 (ja)	2014-11-05	酸性ホスファターゼ及びそれをコードする核酸、並びにこれらを利用したリボフラビン−５’−リン酸の製造方法
JPH01153090A (ja)	1989-06-15	固定化酵素および固定化酵素を用いたエステル合成方法